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How Obama, America’s 250th Year and a Super Bowl Ad Led to Larry David’s New HBO Sketch Comedy Series

June 27, 2026
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How Obama, America’s 250th Year and a Super Bowl Ad Led to Larry David’s New HBO Sketch Comedy Series

When Larry David is pitched an idea, his immediate inclination is to reject it. So much so, that his longtime writing and producing partner Jeff Schaffer referred to him as “the fastest no in show business.”

But when former President Barack Obama and First Lady Michelle Obama’s Higher Ground asked if he’d do a project for America’s 250th anniversary, the fastest no in show business held his trigger finger. That initial ask would turn into the comedy sketch show “Life, Larry and the Pursuit of Unhappiness,” which drops TV’s favorite curmudgeon into history’s biggest moments.

“He was like, ‘Huh, that’s really interesting.’ And Larry is a history buff. He studied American history. He loves American history,” Schaffer recalled in an interview with TheWrap. “It seems so weird to combine President Obama and Larry David, but he’s actually the perfect person. I mean, if Woody Allen and Doris Kearns Goodwin had a baby, it would be Larry David. So we just started talking about ideas and what to do, and as we started talking about it, ‘He’s like, yeah, I really want to do this.”

The opportunity had presented itself after David wrapped up “Curb Your Enthusiasm” after 12 seasons and 24 years on HBO. Schaffer revealed that he and David were already considering new TV ideas as well as a movie before Higher Ground came knocking.

“I remember calling Amy Gravitt at HBO, and I just said, ‘Hey, we have something for you. What if I could deliver you a show starring two people that half of America love?’ And she’s like, ‘What are you talking about?’” Schaffer continued. “So Larry and I went in and pitched this thing, and she’s like, ‘Great, let’s do it,’ but I’m not sure everybody knew what we were going to do with it.”

Schaffer believes David’s willingness to return to TV in “Life, Larry and the Pursuit of Unhappiness” actually stemmed from an FTX commercial David did four years ago, where he played himself all throughout time pooh-poohing every good invention that humanity’s ever created.

“I think he remembered how much fun it was being in costume and he forgot how much he hated being in wigs and hair and makeup. He was like, ‘This will be really fun. We’ll do this, we’ll go all the way through history,’” Schaffer said. “So we just started writing out stuff we thought we might want to do, and then we brought it to HBO, and they were like, ‘Great, go for it.’”

While “Life, Larry and the Pursuit of Unhappiness” continues to take advantage of the improv-style format of “Curb,” Schaffer emphasized its meant to look more cinematic.

“We built the Wright flyer. We were in a World War I trench. They’re not shot like ‘Curb,’ they’re little movies,” he said. “I think everyone’s been excited about how elevated the whole thing is, but it’s still very funny.”

But it still relies on a lineup of flashy guest stars, from familiar faces from David’s body of work, including Jerry Seinfeld, Susie Essman, J.B. Smoove and Vince Vaughn, to new collaborators such as Kathryn Hahn, Bill Hader and, yes, even President Obama.

“He killed,” Schaffer said of Obama’s sketch comedy debut. “We got to spend a decent amount of time filming with him and aside from being one of the coolest individuals on the planet, brilliant and an amazing patriot, he’s also a really funny guy. He’s got great timing and he really enjoys annoying Larry and being annoyed by Larry. He was like, ‘When I’m around him, I just start talking like him, he just sucks me into this. I’m not like this with other people, but with him, this is what I’m like.’ From the first meeting we had, they were so fun together. And there’s lines that Larry and I can take no credit for — it’s 100% Barack.”

life-larry-and-the-pursuit-of-unhappiness-larry-david-barack-obama-hbo
Larry David and President Barack Obama in “Life, Larry and the Pursuit of Unhappiness.” (HBO)

And it’s not a Larry David production without airing some grievances, which becomes the central focus in a sketch spoofing the signing of the Declaration of Independence in Friday’s premiere.

“We had such a long list of grievances. They were all written down in the handwritten font, there’s a long list of them. I actually have a giant poster signed by President Obama, which is one of my favorite things that I possess,” Schaffer said when asked if any grievances didn’t make it into the final cut of the premiere. “Let’s put it this way, Larry has more complaints than we could fit into a sketch.”

Still, there’s a number of surprises throughout the series that the show has kept close to the vest. Among them is Samuel L. Jackson, who lends his voice as the show’s narrator.

Jackson’s involvement came about after David and Schaffer had already finished shooting and were contemplating how to organize everything. They would end up coming up with what Schaffer described as “historical Russian roulette,” where Jackson would provide viewers context through fast-paced documentary style lead-ins before each sketch.

“We needed to tell people what what we were doing. Like fill people in on what is the Alamo or what was the Red Scare or whatever. But what that also does is it allows the sketch to be comedy, because you’ve done the setup,” Schaffer said. “We knew we needed a voice that would be instantly recognizable and have the gravitas, but also the bounce and the slap and the excitement, so it didn’t feel like you were sitting in history class. We were like, ‘Who can this be?’ And Larry just said it should be Sam L. Jackson. He was our first choice and we just talked to his people. We said, ‘Look, here’s what it is’ and he’s like ‘Yeah, I’ll do that, I’ll come in for a day’ and he knocked it out of the park. We caught him right before he was going off to do his own TV show. We had to write write 28 of those rapid fire.”

Schaffer remained tight-lipped about other surprises set for future episodes, but said everyone involved in the show “really came to play.”

“The experience I hope the audience has of ‘Oh that’s this person,’ we had the same thing. Every day was different,” he said. “One day you’re in a World War I trench and then you’re in the Boston Tea Party and then the Great Depression. Every day was a completely new movie.”

“Life, Larry and the Pursuit of Unhappiness” airs Fridays at 9 p.m. ET/PT on HBO and HBO Max.

The post How Obama, America’s 250th Year and a Super Bowl Ad Led to Larry David’s New HBO Sketch Comedy Series appeared first on TheWrap.

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